Abstract
Treatment of ( S)-3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazine with trifluoroacetic acid in MeOD results in regioselective deuteration at its C 6-position affording its corresponding ( S)-[6- 2H 2]-isotopomer in excellent yield with no loss of stereochemical integrity at its C 3-stereocentre. The lithium aza-enolate of this deuterated chiral template has been alkylated with a range of substituted benzyl bromides to afford (3 S,6 R)-[6- 2H]-3-isopropyl-6-benzyl-bis-lactim ethers that were hydrolysed to afford their corresponding ( R)-[α- 2H]-phenylalanine methyl esters as hydrochloride salts in good yield.
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